[3+2]-Cycloaddition of α-Diazocarbonyl Compounds with Arenediazonium Salts Catalyzed by Silver Nitrate Delivers 2,5-Disubstituted Tetrazoles

Sergey Chuprun, Dmitry Dar'In, Grigory Kantin, Mikhail Krasavin

Research output

Abstract

[3+2]-Cycloaddition of arenediazonium salts with diazo compounds (earlier exemplified only for trimethylsilyldiazomethane and 2,2,2-trifluorodiazoethane) has been developed to include a wide range of readily available α-diazocarbonyl compounds. The resulting 2-aryl-5-acyl-2 H -tetrazoles are of high value in medicinal chemistry.

Original languageEnglish
Pages (from-to)3998-4005
JournalSynthesis (Germany)
Volume51
Issue number21
Early online date12 Aug 2019
DOIs
Publication statusPublished - 2019

Fingerprint

Tetrazoles
Silver Nitrate
Cycloaddition
Nitrates
Silver
Salts
trimethylsilyldiazomethane
Pharmaceutical Chemistry
2,2,2-trifluorodiazoethane

Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

@article{e15531b1625743b7a23ae87c642b8a60,
title = "[3+2]-Cycloaddition of α-Diazocarbonyl Compounds with Arenediazonium Salts Catalyzed by Silver Nitrate Delivers 2,5-Disubstituted Tetrazoles",
abstract = "[3+2]-Cycloaddition of arenediazonium salts with diazo compounds (earlier exemplified only for trimethylsilyldiazomethane and 2,2,2-trifluorodiazoethane) has been developed to include a wide range of readily available α-diazocarbonyl compounds. The resulting 2-aryl-5-acyl-2 H -tetrazoles are of high value in medicinal chemistry.",
keywords = "arenediazonium tosylates, silver nitrate, tetrazoles, [3+2]-cycloaddition, α-diazocarbonyl compounds, 5-SUBSTITUTED 1H-TETRAZOLES, ACID, ISOCYANIDES, DIAZO-COMPOUNDS, REGIOSELECTIVE 3+2 CYCLOADDITION, MEDICINAL CHEMISTRY, NITRILES, alpha-diazocarbonyl compounds, DIAZOKETONES, INHIBITORS, ACCESS",
author = "Sergey Chuprun and Dmitry Dar'In and Grigory Kantin and Mikhail Krasavin",
year = "2019",
doi = "10.1055/s-0039-1690159",
language = "English",
volume = "51",
pages = "3998--4005",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "21",

}

TY - JOUR

T1 - [3+2]-Cycloaddition of α-Diazocarbonyl Compounds with Arenediazonium Salts Catalyzed by Silver Nitrate Delivers 2,5-Disubstituted Tetrazoles

AU - Chuprun, Sergey

AU - Dar'In, Dmitry

AU - Kantin, Grigory

AU - Krasavin, Mikhail

PY - 2019

Y1 - 2019

N2 - [3+2]-Cycloaddition of arenediazonium salts with diazo compounds (earlier exemplified only for trimethylsilyldiazomethane and 2,2,2-trifluorodiazoethane) has been developed to include a wide range of readily available α-diazocarbonyl compounds. The resulting 2-aryl-5-acyl-2 H -tetrazoles are of high value in medicinal chemistry.

AB - [3+2]-Cycloaddition of arenediazonium salts with diazo compounds (earlier exemplified only for trimethylsilyldiazomethane and 2,2,2-trifluorodiazoethane) has been developed to include a wide range of readily available α-diazocarbonyl compounds. The resulting 2-aryl-5-acyl-2 H -tetrazoles are of high value in medicinal chemistry.

KW - arenediazonium tosylates

KW - silver nitrate

KW - tetrazoles

KW - [3+2]-cycloaddition

KW - α-diazocarbonyl compounds

KW - 5-SUBSTITUTED 1H-TETRAZOLES

KW - ACID

KW - ISOCYANIDES

KW - DIAZO-COMPOUNDS

KW - REGIOSELECTIVE 3+2 CYCLOADDITION

KW - MEDICINAL CHEMISTRY

KW - NITRILES

KW - alpha-diazocarbonyl compounds

KW - DIAZOKETONES

KW - INHIBITORS

KW - ACCESS

UR - http://www.scopus.com/inward/record.url?scp=85073752880&partnerID=8YFLogxK

U2 - 10.1055/s-0039-1690159

DO - 10.1055/s-0039-1690159

M3 - Article

AN - SCOPUS:85073752880

VL - 51

SP - 3998

EP - 4005

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 21

ER -